potassium hydroxide in methanol Ambient temperature; Yield given;

1: 1) n-butyllithium / 1) THF, 2) -70 deg C 2: 85 percent / K2CO3 / dimethylformamide / Ambient temperature 3: 78 percent / NaNO2, acetic acid / ethanol / 0.5 h 4: 1.2 g / Zn, formic acid / tetrahydrofuran; H2O / 1 h / 0 - 5 °C 5: 1M KOH / methanol / Ambient temperature View Scheme

1: 44 percent / EtONa / ethanol 2: 89 percent / K2CO3 / aq. ethanol / 8 h / Heating 3: 85 percent / K2CO3 / dimethylformamide / Ambient temperature 4: 78 percent / NaNO2, acetic acid / ethanol / 0.5 h 5: 1.2 g / Zn, formic acid / tetrahydrofuran; H2O / 1 h / 0 - 5 °C 6: 1M KOH / methanol / Ambient temperature View Scheme

1: 1) 48percent HBr, Br2, 2) NaNO2 / 2) water, 0 deg C, 30 min 2: 44 percent / EtONa / ethanol 3: 89 percent / K2CO3 / aq. ethanol / 8 h / Heating 4: 85 percent / K2CO3 / dimethylformamide / Ambient temperature 5: 78 percent / NaNO2, acetic acid / ethanol / 0.5 h 6: 1.2 g / Zn, formic acid / tetrahydrofuran; H2O / 1 h / 0 - 5 °C 7: 1M KOH / methanol / Ambient temperature View Scheme

1: 89 percent / K2CO3 / aq. ethanol / 8 h / Heating 2: 85 percent / K2CO3 / dimethylformamide / Ambient temperature 3: 78 percent / NaNO2, acetic acid / ethanol / 0.5 h 4: 1.2 g / Zn, formic acid / tetrahydrofuran; H2O / 1 h / 0 - 5 °C 5: 1M KOH / methanol / Ambient temperature View Scheme

1: 85 percent / K2CO3 / dimethylformamide / Ambient temperature 2: 78 percent / NaNO2, acetic acid / ethanol / 0.5 h 3: 1.2 g / Zn, formic acid / tetrahydrofuran; H2O / 1 h / 0 - 5 °C 4: 1M KOH / methanol / Ambient temperature View Scheme

1: 78 percent / NaNO2, acetic acid / ethanol / 0.5 h 2: 1.2 g / Zn, formic acid / tetrahydrofuran; H2O / 1 h / 0 - 5 °C 3: 1M KOH / methanol / Ambient temperature View Scheme

1: 1.2 g / Zn, formic acid / tetrahydrofuran; H2O / 1 h / 0 - 5 °C 2: 1M KOH / methanol / Ambient temperature View Scheme